Apartment holiday rentals in West Loop, Chicago

We had an incredible stay in Chicago’s West Loop last week! The place was spotlessly clean and perfectly located, just steps away from fantastic restaurants, bars, and the vibrant heart of the West Loop. The digital keypad on the door made getting in and out incredibly easy, and the building felt very safe. The host was exceptional—clear instructions, always reachable, and stayed in touch throughout our trip to ensure everything went smoothly. Highly recommend this spot for anyone visiting Chicago!

Very responsive and helpful hosts. The place was exactly as described. Would definitely recommend!

Beautiful place. Clean, modern, fully equipped. Roomy bathroom, to boot One block to the CTA (subway) and as an added bonus, that line (Blue) goes straight to O'Hare when it's time to leave! Bus stop right outside the door, too. Starbucks, 7-11, and Guinness brewery/restaurant (and local bars) within a couple of blocks. Overall, it is a great jumping off point for exploring Chicago as it is just outside the Loop area (one stop on the CTA). We would use this place again when coming to town!

Beautiful view especially at sunset and night time. And great restaurants nearby.

Stayed here for 2 weeks for a work trip. It feels just like staying in your own apartment. I love that they allow pets. It’s pricey (keep in mind there are additional charges for pets and for parking), but for the location and quality of the place I think it is a good value.

Great location. Near grocery store, great restaurants in the heart of Pilsen, and the green/pink line to get to downtown Chicago.

Good things: Host always responded quickly, fabulous view, very sunny, gorgeous sunsets, comfortable place, easy walks to the riverwalk and Fulton market, grocery store very close. just a fun, active place to be! Challenges: a bad smell randomly came up from the kitchen sink and maintenance could not fix it, so we burned candles; no a/c available bc it gets turned on (switched over from heat) when the whole building switches it which made it quite warm some days in April; only had one key for the two of us which made it hard to split up and do different things; saw 1 cockroach, but pest control took care of it immediately and there were never anymore, and we stayed there 1 month!...just being honest here because some of the 5 star reviews are not completely honest. We would stay here again, despite the challenges!

We had a great stay. The apartment is very cool - expansive loft with plenty of room to work and relax.

The place was great for my stay. The pictures don’t do justice as to how well it’s decorated. I’m a bookworm/nerd so I appreciated the books that were on-hand to read. The shower & kitchen was amazing as well. The place itself was peaceful and neighborhood was quiet and walkable. Will definitely be booking again in the future. Thanks Dean!

An absolutely fantastic location and cozy airbnb for my sister and I’s trip to Chicago to see Beyoncé. Tons of restaurants a short walk and drive away, there’s a train station 3 blocks away as well, and Dark Star coffee was a great rec. Loved the airbnb, it may look small but it is so spacious. We each had our own amount of privacy and didn’t feel on top of each other. Only thing that I would recommend is packing on the lighter side for there are quite a few steps to climb to get up to the airbnb. But all in all worth it. Definitely bookmarking their place for future Chicago visits.

I had a great time staying here. Not only does it look exactly like the pictures, but it was even more spacious than it seems in photos. The cleanliness of the space was pristine and spotless. The location is great too; there’s a train station basically a few steps out the front door. There were plenty of amenities including kitchenware, laundry, and toiletries. Matthew was very helpful in giving detailed instructions for check in as well as tips for places to check out in Chicago and the surrounding neighborhood. He was responsive and timely when I had any questions regarding my stay. I will definitely be booking with Matthew again as he has a ton of other awesome listings and I thoroughly enjoyed my experience here!

Very happy with our stay. Host was easy to work with and quick to respond. The unit is beautiful and nicely equipped. The views and building amenities were great. Had planned to do a lot of Ubering, but the abundance of good food & drink in this cool West Loop neighborhood, and the ease of getting everywhere by train made that unnecessary. Highly recommend!

We loved our stay at Jon's place! The apartment was clean and comfortable & the balcony was an added bonus! The location is awesome - I have visited Chicago many times and this was probably my favorite airbnb that I've stayed in because of access to some of the best restaurants in the city. It's a really charming neighborhood and walkable to tons of restaurants, bakeries, and vintage shops. Jon was an awesome host, I would definitely stay here again!

The place is great! I've stayed numerous times before and it never disappoints. The washer/dryer in the unit is a huge plus! Very close to the blue line and many restaurants walking distance. My favorite bakery is just down the street, D'Amato's. I'm looking forward to staying again soon.

My husband and I loved staying at Brad’s place for our honeymoon! It was such a great location. It is right by the train so I appreciate that earplugs were provided to sleep! I would definitely recommend figuring out parking before you get there. We tried to figure it out when we got there, the spot hero app wasn’t working, it was weird! But if you have parking figured out, it’s the best place to stay! We might make this a yearly stop for us!

This spot was absolutely perfect for our trip! The blue line stop was an easy walk away, there were plenty of restaurants and coffee shops less than 5 minutes away, and even a walkable grocery store with a pharmacy. Ubers/Lyfts are also super easy. The space was spotlessly clean from top to bottom, check-in was seamless, and the hosts left a lovely little guidebook with local recommendations and helpful tips.

Thank you so much, Matthew! The beds were comfortable, the BNB was extremely clean, but still felt the coziness of Home. The hot tub definitely was the highlight of our wind down at night. We will be booking again!

Perfect location for a family to stay that’s close to everything. We did days in the city and a game at Wrigley. Very clean and perfect for our long weekend in Chicago.

I booked this Air BNB for my girlfriend's birthday weekend and my surprise proposal! Ashlee was very responsive, super helpful, just an overall great host! She went out of her way to decorate the master bedroom for me with rose petals, tea lights, champagne and all! There were snacks in the kitchen, the place was clean and tidy, our group really felt at home! The vibes were everything, and so were the VIEWS from the rooftop!!!! Thank you Ashlee!!

We had a good stay and David communicated very well with help that was needed. Good place to stay with anyone traveling with a small child. Thank you!

We stayed with my family for 3 days n loved the place it's ambience, cleanliness, very well equipped with all the necessities.....this place definitely feels like home and the hosts are very kind and quick with there response. Wherever in future I am coming to chicago shall book this place.

Let me just say, the pictures don’t do this cute, cozy place justice! I’m big on hospitality and customer service, and Johana and Akos were beyond accommodating and communicative. I would dare to say this is the most accommodating place I’ve experienced so far! The space has such a good energy and flow to it — cozy, inviting, and with a beautiful sunset view from the kitchen window that you can enjoy right from the living room sofa. The views are stunning, and the building itself is upscale, clean, and even smells great! I enjoy playing some of the games that were pervaded( Uno and Jenga) and I appreciated that the TVs had all the apps, HBO, Disney, prime, Netflix etc. It’s in a great location, and I felt very safe throughout my stay. The only con would be some city noise, but it didn’t bother me at all. There’s a nearby train that doesn’t pass often, and again, it wasn’t an issue for me. I would definitely recommend this place!!

We had a great stay at this apartment in Lincoln Park. The view was excellent, and the building amenities were a nice bonus. The location was convenient too--Whole Foods was right across the street, with other shops like REI nearby. It was easy to get downtown and explore other parts of Lincoln Park. We were traveling with a toddler and a newborn, and the host helped by providing a pack 'n play. Communication was clear and timely. Overall, a smooth experience.

Really loved our stay! Bikes nearby to get around to other parks of the city. Close to what we needed it to be. Very clean. Amenities were amazing! We loved the pool and got tub. Super dog friendly. We’d definitely bring our dog in the future 🥰